EP0649877A2 - Compositions autolubrifiantes - Google Patents
Compositions autolubrifiantes Download PDFInfo
- Publication number
- EP0649877A2 EP0649877A2 EP94116179A EP94116179A EP0649877A2 EP 0649877 A2 EP0649877 A2 EP 0649877A2 EP 94116179 A EP94116179 A EP 94116179A EP 94116179 A EP94116179 A EP 94116179A EP 0649877 A2 EP0649877 A2 EP 0649877A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- phosphoric acid
- mixtures according
- acid ester
- weight
- silicone rubber
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- -1 aryl phosphoric acid ester Chemical class 0.000 claims abstract description 58
- 229920002379 silicone rubber Polymers 0.000 claims abstract description 16
- 239000004945 silicone rubber Substances 0.000 claims abstract description 13
- 239000000654 additive Substances 0.000 claims abstract description 11
- 230000000996 additive effect Effects 0.000 claims abstract description 7
- 229920001296 polysiloxane Polymers 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000004971 Cross linker Substances 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000004073 vulcanization Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 18
- 238000003860 storage Methods 0.000 description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229910019213 POCl3 Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- AGKBXKFWMQLFGZ-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzenecarboperoxoate Chemical compound C1=CC(C)=CC=C1C(=O)OOC(=O)C1=CC=C(C)C=C1 AGKBXKFWMQLFGZ-UHFFFAOYSA-N 0.000 description 1
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
- QTOPEXFOLGHYPX-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-5-methylheptane Chemical compound CC(C)(C)OOC(C)(CC)CCC(C)OOC(C)(C)C QTOPEXFOLGHYPX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004890 Hydrophobing Agent Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- WYUIWUCVZCRTRH-UHFFFAOYSA-N [[[ethenyl(dimethyl)silyl]amino]-dimethylsilyl]ethene Chemical compound C=C[Si](C)(C)N[Si](C)(C)C=C WYUIWUCVZCRTRH-UHFFFAOYSA-N 0.000 description 1
- BUEPLEYBAVCXJE-UHFFFAOYSA-N [ethenyl-methyl-(trimethylsilylamino)silyl]ethene Chemical compound C(=C)[Si](N[Si](C)(C)C)(C=C)C BUEPLEYBAVCXJE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 1
- GBAJYMPPJATTKV-UHFFFAOYSA-N butyl(trifluoro)silane Chemical compound CCCC[Si](F)(F)F GBAJYMPPJATTKV-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000019241 carbon black Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
Definitions
- the present invention relates to mixtures with self-lubricating properties in the cured state, comprising at least one crosslinkable silicone rubber a), at least one aryl phosphoric acid ester b) and at least one further additive c), a process for their preparation and moldings based on these mixtures.
- Self-lubricating silicones are known per se: According to EP 369 255 (Description of the Prior Art), for example, copolymers with diethylsiloxy and diphenylsiloxy units with a significant proportion of diphenylsiloxy groups are only suitable for this purpose to a limited extent, since the exudation behavior is often unpredictable and the lubricating effect is often absent.
- Short-chain OH-terminated diorganosiloxanes with trifluoropropyl groups in peroxidically crosslinked systems should not have this disadvantage (EP 369 255).
- OH-terminated oils are not suitable for addition-crosslinking silicone rubbers which contain hydrogen siloxanes as crosslinkers.
- the OH-terminated polymers also react with the hydrogen siloxanes to form an SiOSi bond: ⁇ Si ⁇ OH + H ⁇ Si ⁇ ⁇ ⁇ Si-O-Si ⁇ + H2 They are integrated into the network and can no longer migrate to the surface and form a lubricating film there.
- both types of oil have other disadvantages. They consist of polymers of different chain lengths, which inevitably cause fluctuating molecular weight distributions. Accordingly, the sweating behavior fluctuates more or less strongly.
- Another disadvantage for technical use is the high prices of these special silicone oils.
- the object of the present invention is therefore to provide mixtures which, in the hardened state, have self-lubricating properties.
- the present invention relates to mixtures with self-lubricating properties in the cured state which contain at least one silicone rubber a), at least one aryl phosphoric acid ester b) and at least one further additive c) in which the aryl phosphoric acid ester used is incompatible with silicone.
- Silicone rubbers a) for the purposes of the invention are substances known per se, as described, for example, in W. Noll "Chemistry and Technology of Silicones", 1968, page 246.
- Component a) preferably corresponds to a silicone rubber of the following formula (II) wherein R and R 'are alkyl radicals with 1 to 8 carbon atoms, aryl radicals, vinyl radicals and fluoroalkyl radicals with 3 to 8 carbon atoms, so that the polymer contains 0.0002 to 3 wt .-% vinyl groups, and x is varied so that the viscosity of the Polymers ranges from 0.1 to 30,000 Pa.s,
- the silicone rubber may optionally contain fillers and water repellents.
- Hydrophobing agents in the sense of the invention are preferably silanol-containing silicone compounds with a viscosity of 0.01 to 1 Pa.s and / or hexaalkyldisilazanes, the organic groups being selected from alkyl radicals with 1 to 8 carbon atoms, vinyl radicals, aryl radicals and fluoroalkyl radicals with 3 to 8 carbon atoms that the silicone compounds have a silanol content (content of S: OH groups) of 2 to 10 wt .-%.
- Suitable fillers for the process according to the invention are e.g. pyrogenic or precipitated, finely divided silicas with a BET surface area of 50 to 500 m2 / g.
- Such fillers can be surface modified, e.g. with organosilicon compounds. The modification can also be carried out during incorporation into the polymer by adding e.g. Hexamethyldisilazane and / or 1,3-divinyl-1,1,3,3-tetramethyldisilazane can be achieved with the addition of water.
- Substances such as diatomaceous earth, finely divided quartz powder, amorphous silicas or carbon blacks can also be used as fillers.
- the silicone rubber a) can be both an addition-crosslinking silicone rubber with hydrogen siloxane as crosslinker a ') and a peroxidically crosslinkable silicone rubber a' ').
- the mixture preferably contains the hydrogen siloxanes described below as crosslinkers where R 'are alkyl radicals with 1 to 8 carbon atoms or aryl and fluoroalkyl radicals with 3 to 8 C atoms, m ⁇ 3 and n + m varies so that the polymer has a viscosity of 0.005 to 1 Pa.s, and additionally one Rhodium or platinum catalyst and possibly inhibitors and other auxiliaries.
- the platinum catalysts are the catalysts usually used for the addition-crosslinking systems, in particular Pt (0) complexes with vinylsiloxanes as ligands.
- Suitable inhibitors are acetylenic alcohols such as 2-methylbutin (3) -ol- (2), ethinylcyclohexanol, tetramethyltetravinylcyclotetrasiloxane or tetramethyldivinyldisiloxane.
- Peroxidically crosslinking compositions preferably contain alkyl or aryl peroxides, such as, for example, the hydrogen siloxanes and the catalyst.
- alkyl or aryl peroxides such as, for example, the hydrogen siloxanes and the catalyst.
- the aryl phosphoric acid esters used according to the invention are generally commercially available products.
- the aryl phosphoric acid ester b) preferably has the general formula (I) in the R1 and R2 phenyl, alkylphenyl, ⁇ -methylbenzylphenyl, alkyl radicals and R3 is phenyl, alkylphenyl, ⁇ -methylbenzylphenyl.
- alkyl radicals linear C1-C8 radicals are preferably used.
- Additives c) in the sense of the invention are preferably unreactive, non-inhibiting, silicone-incompatible oils, such as, for example, trifluoropropylmethyl silicone oil, paraffin oil and plasticizer oils, such as adipic acid esters and polyesters.
- silicone-incompatible oils such as, for example, trifluoropropylmethyl silicone oil, paraffin oil and plasticizer oils, such as adipic acid esters and polyesters.
- the level of addition of aryl phosphoric acid ester b) depends essentially on the hardness of the vulcanizate and the desired amount of exudation as well as the degree of incompatibility of the aryl phosphoric acid ester.
- the amount of the aryl phosphoric acid ester is preferably 0.5 to 10% by weight, particularly preferably 3 to 10% by weight, the amount of the additives is preferably 0.5 to 5% by weight, based on the total mixture.
- the present invention also relates to a process for the preparation of these silicone compositions, according to which components a) to c) are stirred together.
- the present invention also relates to moldings with self-lubricating properties, which can be obtained by introducing components a) and b) and optionally c) into a mold and subsequent vulcanization at elevated pressure and a temperature of 50 to 250 ° C.
- this silicone base composition are mixed with 1.53 g of a trimethylsilyl end-blocked polyorganosiloxane crosslinking agent with an average of 5 methylhydrogensiloxane units and 3 dimethylsiloxane units per molecule, 0.15 g of a platinum catalyst in the form of a complex of chloroplatinic acid with symmetrical divinyltetramethyldisiloxane and containing about 0.65% platinum and about 0.65% platinum and , 02 g of 3,5-dimethyl-1-hexin-3-ol as an inhibitor and 1.5 parts of diphenyl cresyl phosphate are mixed and cured under pressure for 10 minutes at 175 ° C. in a 2 mm thick mold. After storage for 1 day at room temperature, the surface
- a dimethylpolysiloxane (0.02% vinylsiloxy units) with a chain length of 6000 units and a viscosity of 20.106 mPas, ends limited by trimethylsiloxy groups, are mixed with 53.5 parts by weight of a silica with a BET surface area of 200 m2 / g in a kneader at 150 ° C.
- a siloxanol with 18% SiOH groups and 4.2 parts of a siloxanol, which additionally contains 5% vinylmethylsiloxy units, and 0.55 parts of hexamethyldisilazane are added.
- Example 11 but additionally with 1.0 part of diphenyl cresyl phosphate. After storage for 1 day at room temperature, the surface is covered with a thin film of oil.
- Example 11 As in Example 11, but with 0.5 part of copolymer oil (from Example 11) and additionally 1.1 parts of diphenyl cresyl phosphate. After storage for 1 day at room temperature, the surface is covered with a thin film of oil.
- Example 11 As in Example 11, but with 1.9 parts of copolymer oil (from Example 11). After storage for 1 day at room temperature, the surface shows fluctuating properties from dry to slightly lubricating.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4336472 | 1993-10-26 | ||
| DE4336472 | 1993-10-26 | ||
| DE4408660 | 1994-03-15 | ||
| DE4408660A DE4408660A1 (de) | 1993-10-26 | 1994-03-15 | Mischungen mit selbstschmierenden Eigenschaften |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0649877A2 true EP0649877A2 (fr) | 1995-04-26 |
| EP0649877A3 EP0649877A3 (fr) | 1996-05-01 |
| EP0649877B1 EP0649877B1 (fr) | 2001-03-28 |
Family
ID=25930721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94116179A Expired - Lifetime EP0649877B1 (fr) | 1993-10-26 | 1994-10-13 | Compositions autolubrifiantes |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5583170A (fr) |
| EP (1) | EP0649877B1 (fr) |
| JP (1) | JPH07179759A (fr) |
| AT (1) | ATE200099T1 (fr) |
| CA (1) | CA2134042A1 (fr) |
| DE (2) | DE4408660A1 (fr) |
| ES (1) | ES2156887T3 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001090230A1 (fr) * | 2000-05-26 | 2001-11-29 | Nkt Research A/S | Polymeres autolubrifiants |
| WO2005054370A3 (fr) * | 2003-12-03 | 2006-01-05 | Clariant Gmbh | Agents antimousse |
| EP1958988A1 (fr) | 2007-02-15 | 2008-08-20 | Wacker Chemie AG | Compositions de silicone réticulables par addition présentant und faible coefficient de friction |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6871838B2 (en) * | 2003-04-03 | 2005-03-29 | B. Braun Medical Inc. | Injection port valve |
| US7205050B2 (en) * | 2003-06-09 | 2007-04-17 | Permatex, Inc. | Low shear adhesion RTV silicone |
| US7527703B2 (en) * | 2004-09-09 | 2009-05-05 | Jeffrey Swain | Submerged masonry surface treating method |
| JP7359861B2 (ja) | 2019-03-29 | 2023-10-11 | ダウ シリコーンズ コーポレーション | シリコーンエラストマー組成物及びエラストマー材料 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3288743A (en) * | 1966-11-29 | Plasticized polyorganosilsesquioxane compositions | ||
| US2618600A (en) * | 1948-07-15 | 1952-11-18 | Douglas Aircraft Co Inc | Silicone oil lubricating composition |
| US2684336A (en) * | 1950-06-02 | 1954-07-20 | Douglas Aircraft Co Inc | Silicone lubricant containing trialkyl phosphate |
| DE2535334B2 (de) * | 1975-08-07 | 1978-09-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur homogenen Verteilung hochdisperser aktiver Füllstoffe in Poly organosiloxanen |
| DE2708447A1 (de) * | 1976-03-06 | 1977-09-08 | Ciba Geigy Ag | Flammhemmende polymerzusammensetzungen |
| DE2653499C3 (de) * | 1976-11-25 | 1980-05-08 | Wacker-Chemie Gmbh, 8000 Muenchen | Unter Ausschluß von Wasser lagerfähige bei Zutritt desselben bei Raumtemperatur zu Elastomeren vernetzende Organopolysiloxanformmassen |
| JPS57141476A (en) * | 1981-02-25 | 1982-09-01 | Haraden Koji Kk | Refractory airtight sealing material |
| US4497692A (en) * | 1983-06-13 | 1985-02-05 | International Business Machines Corporation | Laser-enhanced jet-plating and jet-etching: high-speed maskless patterning method |
| JPS6241263A (ja) * | 1985-08-16 | 1987-02-23 | Shin Etsu Chem Co Ltd | 動的疲労耐久性シリコ−ンゴム組成物 |
| DE59000647D1 (de) * | 1989-07-20 | 1993-02-04 | Duering Ag | Faltbare kunststoff-flasche. |
| DE4016417A1 (de) * | 1990-05-22 | 1991-11-28 | Bayer Ag | Flammwidrige polycarbonate |
| DE69223550T2 (de) * | 1991-05-28 | 1998-04-16 | Denki Kagaku Kogyo Kk | Flammhemmende Harzzusammensetzung |
| US5412014A (en) * | 1992-06-29 | 1995-05-02 | Dow Corning Corporation | Fire retardant resin compositions |
-
1994
- 1994-03-15 DE DE4408660A patent/DE4408660A1/de not_active Withdrawn
- 1994-10-13 AT AT94116179T patent/ATE200099T1/de not_active IP Right Cessation
- 1994-10-13 DE DE59409702T patent/DE59409702D1/de not_active Expired - Lifetime
- 1994-10-13 EP EP94116179A patent/EP0649877B1/fr not_active Expired - Lifetime
- 1994-10-13 ES ES94116179T patent/ES2156887T3/es not_active Expired - Lifetime
- 1994-10-21 CA CA002134042A patent/CA2134042A1/fr not_active Abandoned
- 1994-10-24 JP JP6282398A patent/JPH07179759A/ja active Pending
-
1995
- 1995-10-06 US US08/539,493 patent/US5583170A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001090230A1 (fr) * | 2000-05-26 | 2001-11-29 | Nkt Research A/S | Polymeres autolubrifiants |
| WO2005054370A3 (fr) * | 2003-12-03 | 2006-01-05 | Clariant Gmbh | Agents antimousse |
| EP1958988A1 (fr) | 2007-02-15 | 2008-08-20 | Wacker Chemie AG | Compositions de silicone réticulables par addition présentant und faible coefficient de friction |
| DE102007007569A1 (de) | 2007-02-15 | 2008-08-21 | Wacker Chemie Ag | Additionsvernetzbare Siliconmassen mit geringen Reibungskoeffizienten |
| US7803868B2 (en) | 2007-02-15 | 2010-09-28 | Wacker Chemie Ag | Addition-crosslinkable silicone compositions with low coefficients of friction |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2156887T3 (es) | 2001-08-01 |
| ATE200099T1 (de) | 2001-04-15 |
| EP0649877B1 (fr) | 2001-03-28 |
| EP0649877A3 (fr) | 1996-05-01 |
| JPH07179759A (ja) | 1995-07-18 |
| DE59409702D1 (de) | 2001-05-03 |
| US5583170A (en) | 1996-12-10 |
| DE4408660A1 (de) | 1995-04-27 |
| CA2134042A1 (fr) | 1995-04-27 |
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